JP7587845B2 - COMPOUND, ORGANIC OPTOELECTRONICS DEVICE AND DISPLAY DEVICE - Google Patents

Description

This application claims the benefit of the filing date of Korean Patent Application No. 10-2019-0012107, filed with the Korean Intellectual Property Office on January 30, 2019, the entire contents of which are incorporated herein by reference.
The present application relates to compounds, organic optoelectronic devices and displays.

An organic optoelectronic diode is an element capable of converting electrical energy and optical energy into each other.
Organic optoelectronic devices are roughly divided into two types based on their operating principle: one is a photoelectric device in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy, and the other is a light-emitting device in which a voltage or current is supplied to electrodes to generate light energy from electrical energy.

Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.
Among these, organic light emitting diodes (OLEDs) have been attracting much attention in recent years due to the increasing demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by the organic material located between electrodes.
An organic light-emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to an organic light-emitting device having such a structure, electrons and holes injected from the two electrodes combine in the organic thin film to form pairs, and then disappear, emitting light. The organic thin film may be configured as a single layer or multiple layers as required.

The material of the organic thin film may have a light-emitting function as necessary. For example, the organic thin film material may be a compound that can constitute a light-emitting layer by itself, or a compound that plays the role of a host or dopant in a host-dopant type light-emitting layer.
In addition, compounds that play a role of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, etc. may be used as materials for the organic thin film.
In order to improve the performance, lifetime or efficiency of organic light emitting devices, there is a continuing need to develop materials for organic thin films.

One embodiment provides compounds that can enable highly efficient and long-life organic optoelectronic devices.
Another embodiment provides an organic optoelectronic device comprising the compound.
Yet another embodiment provides a display device including the organic optoelectronic device.

前記化学式１において、Ｘ^４およびＸ^５のいずれか１つは、－Ｎ－であり、残りのいずれか１つは、－Ｃ（Ｌ^３）_ｎ３Ａｒ^３－であり、
Ａｒ^３は、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｘ^１～Ｘ^３は、互いに独立して、－Ｃ（Ｌ^４）_ｎ４Ａｒ^４－；－Ｃ（Ｌ^５）_ｎ５Ａｒ^５－；－Ｏ－；または－Ｓ－であり、Ｘ^１～Ｘ^３のいずれか１つは、－Ｏ－；または－Ｓ－であり、
Ａｒ^４およびＡｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１およびＡｒ^２は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 In one embodiment of the present invention, there is provided a compound represented by the following Formula 1:

In the formula 1, any one of ^X4 and ^X5 is -N-, and ^the remaining one is -C( ^L3 ) _n3Ar3- ;
^Ar3 is hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
X ¹ to X ³ are each independently -C(L ⁴ ) _n4 Ar ⁴ -; -C(L ⁵ ) _n5 Ar ⁵ -; -O-; or -S-; and any one of X ¹ to X ³ is -O-; or -S-;
Ar ⁴ and Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
Ar ¹ and Ar ² are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
n1 to n5 are each independently an integer from 0 to 4;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

前記化学式２において、Ｘ^１は、－Ｏ－；または－Ｓ－であり、
Ａｒ^１～Ａｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 The compound may be represented by the following formula 2:

In the formula 2, ^X1 is -O-; or -S-;
Ar ¹ to Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 to n5 are each independently an integer from 0 to 4;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

前記化学式３において、Ｘ^１は、－Ｏ－；または－Ｓ－であり、
Ａｒ^１～Ａｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 The compound may be represented by the following formula 3:

In the formula 3, ^X1 is -O-; or -S-;
Ar ¹ to Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 to n5 are each independently an integer from 0 to 4;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

前記化学式４において、Ｘ^１は、－Ｏ－；または－Ｓ－であり、
Ａｒ^１～Ａｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 The compound may be represented by the following formula 4:

In the formula 4, ^X1 is -O-; or -S-;
Ar ¹ to Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 to n5 are each independently an integer from 0 to 4;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

According to another embodiment, there is provided an organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, the organic layer comprising the compound.
According to yet another embodiment, there is provided a display device including the organic optoelectronic device.

It is possible to realize highly efficient and long-life organic optoelectronic devices.

1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment. 1 is a cross-sectional view illustrating an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, preferred embodiments of the present invention will be described in detail by way of example only, and are not intended to limit the present invention, which is defined only by the scope of the claims set forth below.
In this specification, "substituted or unsubstituted" means deuterium; a halogen group; -CN; a C1-C60 linear or branched alkyl group; a C2-C60 linear or branched alkenyl group; a C2-C60 linear or branched alkynyl group; a C3-C60 monocyclic or polycyclic cycloalkyl group; a C2-C60 monocyclic or polycyclic heterocycloalkyl group; a C6-C60 monocyclic or polycyclic aryl group; a C2-C60 monocyclic or polycyclic heteroaryl group; -SiRR'R";-P(=O)RR'; a C1-C2 or is substituted or unsubstituted with one or more substituents selected from the group consisting of a C6-C60 alkylamine group, a C6-C60 monocyclic or polycyclic arylamine group, a C2-C60 monocyclic or polycyclic heteroarylamine group, and a substituted or unsubstituted alkoxy group, or is substituted or unsubstituted with a substituent to which two or more of the above substituents are bonded, or is substituted or unsubstituted with a substituent to which two or more of the above substituents are linked. These may also form an additional ring with adjacent substituents.

For example, the "substituent having two or more substituents linked thereto" may be a biphenyl group. That is, the biphenyl group may be an aryl group and may be interpreted as a substituent having two phenyl groups linked thereto. The additional substituent may be further substituted. The R, R', and R" may be the same or different from each other, and each independently represent hydrogen; deuterium; -CN; a substituted or unsubstituted C1-C60 linear or branched alkyl group; a substituted or unsubstituted C3-C60 monocyclic or polycyclic cycloalkyl group; a substituted or unsubstituted C6-C60 monocyclic or polycyclic aryl group; or a substituted or unsubstituted C2-C60 monocyclic or polycyclic heteroaryl group.

According to one embodiment of the present application, the term "substituted or unsubstituted" means that the compound is substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium, a halogen group, -CN, -SiRR'R", -P(=O)RR', a C1-C20 linear or branched alkyl group, a C6-C60 monocyclic or polycyclic aryl group, and a C2-C60 monocyclic or polycyclic heteroaryl group, and the R, R', and R" may be the same or different from each other and may each be independently substituted with hydrogen; deuterium; -CN; deuterium, a halogen group, -CN, a C1-C20 alkyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group. or unsubstituted C1-C60 alkyl groups; C3-C60 cycloalkyl groups substituted or unsubstituted with deuterium, halogen, -CN, C1-C20 alkyl groups, C6-C60 aryl groups, and C2-C60 heteroaryl groups; C6-C60 aryl groups substituted or unsubstituted with deuterium, halogen, -CN, C1-C20 alkyl groups, C6-C60 aryl groups, and C2-C60 heteroaryl groups; or C2-C60 heteroaryl groups substituted or unsubstituted with deuterium, halogen, -CN, C1-C20 alkyl groups, C6-C60 aryl groups, and C2-C60 heteroaryl groups.

The term "substituted" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent, and the position of the substitution is not limited as long as it is a position at which a hydrogen atom is substituted, i.e., a position at which a substituent can be substituted, and when two or more substituents are substituted, the two or more substituents may be the same or different.
In this specification, the halogen may be fluorine, chlorine, bromine, or iodine.
In this specification, the alkyl group includes a C1 to C60 straight or branched chain, and may be additionally substituted with other substituents. The number of carbon atoms in the alkyl group may be 1 to 60, specifically 1 to 40, specifically 1 to 10, and more specifically 1 to 20. Specific examples include a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, a tert-butyl group, a sec-butyl group, a 1-methyl-butyl group, a 1-ethyl-butyl group, a pentyl group, a n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a hexyl group, a n-hexyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 4-methyl-2-pentyl group, a 3,3-dimethylbutyl group, a 2-ethylbutyl group, a heptyl group, a 2-methylpentyl group, a 2-ethylbutyl group, a 2-methylpentyl ... Examples of such alkyl groups include, but are not limited to, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, and 5-methylhexyl.

In this specification, the alkenyl group includes a C2-C60 linear or branched chain, which may be additionally substituted with other substituents. The number of carbon atoms in the alkenyl group may be 2-60, specifically 2-40, and more specifically 2-20. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

As used herein, the alkynyl group includes linear or branched chains of C2 to C60, which may be additionally substituted with other substituents. The number of carbon atoms in the alkynyl group may be 2 to 60, specifically 2 to 40, and more specifically 2 to 20.

In this specification, the cycloalkyl group includes a C3-C60 monocyclic or polycyclic group, and may be additionally substituted with other substituents. Here, polycyclic means a group in which the cycloalkyl group is directly linked or condensed with another cyclic group. Here, the other cyclic group may be a cycloalkyl group, but may also be other types of cyclic groups, such as a heterocycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the cycloalkyl group may be 3 to 60, specifically 3 to 40, and more specifically 5 to 20. Specific examples include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 3-methylcyclopentyl group, a 2,3-dimethylcyclopentyl group, a cyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 3,4,5-trimethylcyclohexyl group, a 4-tert-butylcyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

In this specification, the alkoxy group may be a C1 to C10 alkoxy group, or more specifically, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.

In this specification, the silyl group may be represented by -SiRR'R'', where R, R', and R'' are as defined above. More specifically, -Sidimethylyl, -Sidiethyl, -Simethylethyl, etc. are possible.

In this specification, the phosphine oxide group may be represented by -P(=O)RR', where R and R' are as defined above. More specifically, -P(=O)dimethyl, -P(=O)diethyl, -P(=O)methylethyl, etc. are possible.

In this specification, the term "fluorenyl group" refers to a substituent containing various substituents at the 9th position. Specifically, it is used to mean a fluorenyl group substituted with two hydrogens, two alkyl groups, two aryl groups, or two heteroaryl groups at the 9th position. More specifically, 9-di-H-fluorenyl group, 9-di-methyl-fluorenyl group, 9-di-phenyl-fluorenyl group, etc. can be used.

In this specification, the heterocycloalkyl group includes O, S, Se, N, or Si as a heteroatom, includes a C2-C60 monocyclic or polycyclic ring, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the heterocycloalkyl group is directly linked to or condensed with another cyclic group. Here, the other cyclic group may be a heterocycloalkyl group, but may also be other types of cyclic groups, such as a cycloalkyl group, an aryl group, or a heteroaryl group. The number of carbon atoms in the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, and more specifically 3 to 20.

In this specification, the aryl group includes a C6-C60 monocyclic or polycyclic ring, and may be additionally substituted with other substituents. Here, polycyclic means a group in which an aryl group is directly linked or condensed with another ring group. Here, the other ring group may be an aryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, etc. The aryl group includes a spiro group. The number of carbon atoms in the aryl group may be 6 to 60, specifically 6 to 40, specifically 6 to 30, and more specifically 6 to 25. Specific examples of the aryl group include, but are not limited to, a phenyl group, a biphenyl group, a triphenyl group, a naphthyl group, an anthryl group, a chrysenyl group, a phenanthrenyl group, a perylenyl group, a fluoranthenyl group, a triphenylenyl group, a phenalenyl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, an indenyl group, an acenaphthylenyl group, a benzofluorenyl group, a spirobifluorenyl group, a 2,3-dihydro-1H-indenyl group, and condensed ring groups thereof.

In this specification, the spiro group is a group containing a spiro structure and may be C15 to C60. For example, the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro-bonded to a fluorenyl group. Specifically, the following spiro group may include any one of the groups represented by the following structural formulas:

In this specification, the heteroaryl group includes S, O, Se, N, or Si as a heteroatom, includes a C2-C60 monocyclic or polycyclic ring, and may be additionally substituted with other substituents. Here, the polycyclic ring means a group in which the heteroaryl group is directly linked or condensed with another ring group. Here, the other ring group may be a heteroaryl group, but may also be other types of ring groups, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, etc. The number of carbon atoms in the heteroaryl group may be 2 to 60, specifically 2 to 40, specifically 2 to 30, and more specifically 3 to 25. Specific examples of the heteroaryl group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophene group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a furazanyl group, an oxadiazolyl group, a thiadiazolyl group, a dithiazolyl group, a tetrazolyl group, a pyranyl group, a thiopyranyl group, a diazinyl group, an oxazinyl group, a thiazinyl group, a dioxinyl group, and a triazinyl group. group, tetrazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenanthridinyl group, imidazopyridinyl group, diazanaphthalenyl group, triazaindene group, indolyl group, indolizinyl group, benzothiazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiophene group, benzofuran group, dibenzothiophene group, dibenzofuran group, carbazolyl group, benzocathyl group, carbazolyl group, dibenzocarbazolyl group, phenazinyl group, dibenzosilole group, spirobi(dibenzosilole), dihydrophenazinyl group, phenoxazinyl group, phenanthridyl group, imidazopyridinyl group, thienyl group, indolo[2,3-a]carbazolyl group, indolo[2,3-b]carbazolyl group, indolinyl group, 10,11-dihydro-dibenzo[b,f]azepine group, 9,10-dihydroacridinyl group, phenanthrazinyl group, phenothiazinyl group, Examples include, but are not limited to, azinyl, phthalazinyl, naphthyridinyl, phenanthrolinyl, benzo[c][1,2,5]thiadiazolyl, 5,10-dihydrodibenzo[b,e][1,4]azasilinyl, pyrazolo[1,5-c]quinazolinyl, pyrido[1,2-b]indazolyl, pyrido[1,2-a]imidazo[1,2-e]indolinyl, and 5,11-dihydroindeno[1,2-b]carbazolyl.

In this specification, the amine group may be selected from the group consisting of a monoalkylamine group, a monoarylamine group, a monoheteroarylamine group, -NH ₂ , a dialkylamine group, a diarylamine group, a diheteroarylamine group, an alkylarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, a dibiphenylamine group, an anthracenylamine group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a triphenylamine group, a biphenylnaphthylamine group, a phenylbiphenylamine group, a biphenylfluorenylamine group, a phenyltriphenylenylamine group, and a biphenyltriphenylenylamine group, but are not limited thereto.

In this specification, an arylene group refers to an aryl group having two bonding positions, i.e., a divalent group. The above explanation of the aryl group is applicable to these groups, except that they are both divalent groups. In addition, a heteroarylene group refers to a heteroaryl group having two bonding positions, i.e., a divalent group. The above explanation of the heteroaryl group is applicable to these groups, except that they are both divalent groups.

In this specification, the hole characteristic refers to the ability to donate electrons to form holes when an electric field is applied, and refers to the ability to have conduction characteristics along the HOMO level and to facilitate the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

Examples of substituents having hole properties include substituted or unsubstituted C6 to C60 aryl groups having hole properties, substituted or unsubstituted C2 to C60 heteroaryl groups having hole properties, substituted or unsubstituted arylamine groups, or substituted or unsubstituted heteroarylamine groups.
More specifically, the substituted or unsubstituted C6-C60 aryl group having hole properties may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted perylenyl group, or a combination thereof.

More specifically, the substituted or unsubstituted C2-C60 heteroaryl group having hole properties is a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted indolecarbazolyl group, etc.

The aryl group or heteroaryl group which is a substituent bonded to the nitrogen of the substituted or unsubstituted arylamine group and the substituted or unsubstituted heteroarylamine group is more specifically a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenylyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted phenyl ... a substituted or unsubstituted phenyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted phenyl ... The quinolinyl group may be a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, or a combination thereof.

In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and refer to properties that have conductive properties along the LUMO level and facilitate the injection of electrons formed in the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

The substituted or unsubstituted C2 to C60 heteroaryl group having the electronic properties is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isofuranyl group, a substituted or unsubstituted benzoisofuranyl group, a substituted or unsubstituted oxazoline group, a substituted or unsubstituted benzoxazoline group, a substituted or unsubstituted oxadiazoline group, a substituted or unsubstituted benzoxadiazoline group, a substituted or unsubstituted oxatriazolyl ... The substituted or unsubstituted thiophenyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted isothiazoline group, substituted or unsubstituted benzoisothiazoline group, substituted or unsubstituted thiazoline group, substituted or unsubstituted benzothiazoline group, substituted or unsubstituted pyridazinyl group, substituted or unsubstituted benzopyridazinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted benzopyrazinyl group, substituted or unsubstituted phthalazinyl group, substituted or unsubstituted benzoquinolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted quinazolinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenanthrolinyl group, substituted or unsubstituted phenazinyl group, or a combination thereof.

More specifically, the substituted or unsubstituted C2 to C60 heteroaryl group having the electronic properties may be any one of the following formulas X-1 to X-5:

In one embodiment of the present application, L ⁿ may be a direct bond (or a single bond); a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.
In other embodiments, L ⁿ can be a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

In still other embodiments, L ⁿ can be a direct bond; a substituted or unsubstituted C6 to C40 arylene group; or a substituted or unsubstituted C2 to C40 heteroarylene group.

The n in ^Ln represents a number for distinguishing the substituents.

前記化学式１において、Ｘ^４およびＸ^５のいずれか１つは、－Ｎ－であり、残りのいずれか１つは、－Ｃ（Ｌ^３）_ｎ３Ａｒ^３－であり、
Ａｒ^３は、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｘ^１～Ｘ^３は、互いに独立して、－Ｃ（Ｌ^４）_ｎ４Ａｒ^４－；－Ｃ（Ｌ^５）_ｎ５Ａｒ^５－；－Ｏ－；または－Ｓ－のいずれか１つであり、Ｘ^１～Ｘ^３のいずれか１つは、－Ｏ－；または－Ｓ－であり、
Ａｒ^４およびＡｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１およびＡｒ^２は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 The compound according to one embodiment will be described below.
The compound according to one embodiment is represented by the following formula 1:

In the formula 1, any one of ^X4 and ^X5 is -N-, and ^the remaining one is -C( ^L3 ) _n3Ar3- ;
^Ar3 is hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
X ¹ to X ³ are each independently any one of -C(L ⁴ ) _n4 Ar ⁴ -; -C(L ⁵ ) _n5 Ar ⁵ -; -O-; or -S-; and any one of X ¹ to X ³ is -O-; or -S-;
Ar ⁴ and Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
Ar ¹ and Ar ² are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
n1 to n5 are each independently an integer from 0 to 4;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

The compound represented by Chemical Formula 1 has a structure in which a substituent having electron or hole properties is bonded to a fused ring of a core.
In the compound corresponding to Chemical Formula 1 of the present application, the HOMO/LUMO electron cloud of the fused ring corresponding to the core structure is expanded, and thus the HOMO/LUMO energy level is adjusted to further enhance the hole/electron injection and hole/electron transport capabilities, thereby reducing the driving voltage of a device to which the compound is applied.

In addition, it is possible to synthesize compounds having properties specific to the introduced substituent by introducing various substituents into the structure of Chemical Formula 1. For example, it is possible to synthesize materials that satisfy the requirements for each organic layer by introducing into the core structure substituents that are mainly used in hole injection layer materials, hole transport layer materials, light emitting layer materials, electron transport layer materials, and charge generation layer materials used in the manufacture of an organic light emitting device.
Furthermore, by introducing various substituents into the structure of Formula 1, the energy band gap can be finely adjusted, while the properties at the interface between organic materials can be improved, and the uses of the material can be diversified.

On the other hand, the compound has a high glass transition temperature (Tg) and excellent thermal stability. Such increased thermal stability is an important factor in providing driving stability to the device.

前記化学式２～４において、Ｘ^１は、－Ｏ－；または－Ｓ－であり、
Ａｒ^１～Ａｒ^５は、互いに独立して、水素；重水素；シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^１～Ｌ^５は、互いに独立して、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
ｎ１～ｎ５は、互いに独立して、０～４の整数の１つであり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ａｒ^１～Ａｒ^５の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基である。 More specifically, the compound may be represented by any one of the following chemical formulas 2 to 4.

In the above formulas 2 to 4, X ¹ is -O-; or -S-;
Ar ¹ to Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ⁵ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
n1 to n5 are each independently an integer from 0 to 4;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties.

In one embodiment of the present application, L ¹ to L ⁵ may be, independently of each other, a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group.

In other embodiments, L ¹ -L ⁵ can be, independently of each other, a single bond; a substituted or unsubstituted C6-C40 arylene group; or a substituted or unsubstituted C2-C40 heteroarylene group.

In yet other embodiments, L ¹ to L ⁵ may each independently be a single bond; a C6 to C40 arylene group substituted or unsubstituted with a C2 to C40 heteroaryl group; or a C2 to C40 heteroarylene group substituted or unsubstituted with a C6 to C40 aryl group.

In yet another embodiment, L ¹ to L ⁵ may be, independently of each other, a single bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; a substituted or unsubstituted anthracene group; a substituted or unsubstituted divalent pyrimidine group; a substituted or unsubstituted divalent pyridine group; or a substituted or unsubstituted divalent triazine group.

In still another embodiment, L ¹ to L ⁵ may each independently be a single bond; a phenylene group substituted or unsubstituted with a carbazole group; a biphenylene group; an anthracene group; a divalent pyrimidine group substituted or unsubstituted with a phenyl group; a divalent pyridine group substituted or unsubstituted with a phenyl group; or a divalent triazine group substituted or unsubstituted with a phenyl group.

In one embodiment of the present application, Ar ¹ to Ar ⁵ may each independently be hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In other embodiments, Ar ¹ -Ar ⁵ may each independently be hydrogen; a cyano group; -P(=O)RR'; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group.

In still other embodiments, Ar ¹ -Ar ⁵ may each independently be hydrogen; a cyano group; -P(=O)RR'; a substituted or unsubstituted C6 to C40 aryl group; or a substituted or unsubstituted C2 to C40 heteroaryl group.

In yet another embodiment, Ar ¹ to Ar ⁵ may each independently be hydrogen; a cyano group; -P(=O)RR'; a C6 to C40 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group; or a C2 to C40 heteroaryl group substituted or unsubstituted with one or more substituents selected from the group consisting of a C6 to C40 aryl group and a C2 to C40 heteroaryl group.

In yet another embodiment, Ar ¹ -Ar ⁵ may each independently be hydrogen; a cyano group; -P(=O)RR'; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

In yet another embodiment, Ar ¹ -Ar Each of ^{the 5's} may be, independently, a hydrogen atom; a cyano group; -P(=O)RR'; a phenyl group substituted or unsubstituted with a carbazole group; a naphthyl group; a triphenylenyl group; an anthracenyl group substituted or unsubstituted with a naphthyl group; a terphenyl group; a pyridine group substituted or unsubstituted with a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a triphenylenyl group, a dibenzofuran group, and a dibenzothiophene group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a triphenylenyl group, a dibenzofuran group, and a dibenzothiophene group; a quinazoline group substituted or unsubstituted with a phenyl group or a biphenyl group; a phenanthroline group substituted or unsubstituted with a phenyl group; a benzimidazole group substituted or unsubstituted with a phenyl group; a benzoxazole group; a carbazole group; a dibenzofuran group; or a dibenzothiophene group.

In one embodiment of the present application, Ar ¹ and Ar ² may be hydrogen.

前記化学式２－１～２－３において、
Ｘ^１、Ａｒ^３～Ａｒ^５、Ｌ^３～Ｌ^５、ｎ３～ｎ５の定義は、前記化学式２における定義と同じであり、
Ａｒ^６は、シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^６は、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
Ａｒ^３～Ａｒ^６の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基であり、
ｎ６は、０～４の整数の１つである。 In one embodiment of the present application, the formula 2 may be represented by any one of the following formulas 2-1 to 2-3.

In the above Chemical Formulas 2-1 to 2-3,
The definitions of X ¹ , Ar ³ to Ar ⁵ , L ³ to L ⁵ , and n3 to n5 are the same as those in Chemical Formula 2;
Ar ⁶ is a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
^L6 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
At least one of Ar ³ to Ar ⁶ is a substituent having electronic properties; or a substituent having hole properties;
n6 is an integer from 0 to 4.

前記化学式３－１～３－３において、
Ｘ^１、Ａｒ^３～Ａｒ^５、Ｌ^３～Ｌ^５、ｎ３～ｎ５の定義は、前記化学式３における定義と同じであり、
Ａｒ^６は、シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^６は、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
Ａｒ^３～Ａｒ^６の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基であり、
ｎ６は、０～４の整数の１つである。 In one embodiment of the present application, the formula 3 may be represented by any one of the following formulas 3-1 to 3-3.

In the above Chemical Formulas 3-1 to 3-3,
The definitions of X ¹ , Ar ³ to Ar ⁵ , L ³ to L ⁵ , and n3 to n5 are the same as those in Chemical Formula 3;
Ar ⁶ is a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
^L6 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
At least one of Ar ³ to Ar ⁶ is a substituent having electronic properties; or a substituent having hole properties;
n6 is an integer from 0 to 4.

前記化学式４－１～４－３において、
Ｘ^１、Ａｒ^３～Ａｒ^５、Ｌ^３～Ｌ^５、ｎ３～ｎ５の定義は、前記化学式４における定義と同じであり、
Ａｒ^６は、シアノ基；－Ｐ（＝Ｏ）ＲＲ’；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
前記ＲおよびＲ’は、互いに独立して、水素；置換もしくは非置換のＣ１～Ｃ６０アルキル基；置換もしくは非置換のＣ６～Ｃ６０アリール基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリール基であり、
Ｌ^６は、単結合；置換もしくは非置換のＣ６～Ｃ６０アリーレン基；または置換もしくは非置換のＣ２～Ｃ６０ヘテロアリーレン基であり、
Ａｒ^３～Ａｒ^６の少なくともいずれか１つは、電子特性を有する置換基；または正孔特性を有する置換基であり、
ｎ６は、０～４の整数の１つである。 In one embodiment of the present application, the formula 4 may be represented by any one of the following formulas 4-1 to 4-3.

In the above Chemical Formulas 4-1 to 4-3,
The definitions of X ¹ , Ar ³ to Ar ⁵ , L ³ to L ⁵ , and n3 to n5 are the same as those in Chemical Formula 4.
Ar ⁶ is a cyano group; -P(=O)RR'; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
^L6 is a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
At least one of Ar ³ to Ar ⁶ is a substituent having electronic properties; or a substituent having hole properties;
n6 is an integer from 0 to 4.

In the above examples, the description of the substituents having the above electronic properties is omitted because it overlaps with the description of the substituents described above.

In the above examples, the substituents having hole characteristics are also the same as those described above.

前記化学式５－１～化学式５－４において、Ｘは、－Ｏ－または－Ｓ－であり、Ｒ^ｂ～Ｒ^ｅは、水素、重水素、シアノ基、または置換もしくは非置換のＣ１～Ｃ６０アルキル基である。
前記化学式５－１～５－４において、＊は、結合位置を意味する。
前記化学式５－１～５－４は、化合物全体の正孔、電子特性を考慮して選択可能である。 More specifically, the substituent having hole characteristics may be any one of the following chemical formulas 5-1 to 5-4.

In the above Chemical Formula 5-1 to Chemical Formula 5-4, X is —O— or —S—, and R ^b to R ^e are hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C60 alkyl group.
In the above formulas 5-1 to 5-4, * indicates a bonding position.
The formulas 5-1 to 5-4 can be selected in consideration of the hole and electron properties of the entire compound.

In one embodiment of the present application, the substituent having electronic properties; or the substituent having hole properties may be -P(=O)RR'; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted pyridine group; a substituted or unsubstituted triazine group; a substituted or unsubstituted pyrimidine group; a substituted or unsubstituted quinazoline group; a substituted or unsubstituted phenanthroline group; a substituted or unsubstituted benzimidazole group; a substituted or unsubstituted benzoxazole group; a substituted or unsubstituted carbazole group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
In other embodiments, the substituent having electronic properties or the substituent having hole properties may be -P(=O)RR'; a triphenylenyl group; an anthracenyl group substituted or unsubstituted with a naphthyl group; a terphenyl group; a pyridine group substituted or unsubstituted with a pyridine group; a triazine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a triphenylenyl group, a dibenzofuran group, and a dibenzothiophene group; a pyrimidine group substituted or unsubstituted with one or more substituents selected from the group consisting of a phenyl group, a biphenyl group, a triphenylenyl group, a dibenzofuran group, and a dibenzothiophene group; a quinazoline group substituted or unsubstituted with a phenyl group or a biphenyl group; a phenanthroline group substituted or unsubstituted with a phenyl group; a benzimidazole group substituted or unsubstituted with a phenyl group; a benzoxazole group; a carbazole group; a dibenzofuran group; or a dibenzothiophene group.

In one embodiment of the present application, R and R' may be, independently of each other, hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group.

In other embodiments, R and R' may each independently be a substituted or unsubstituted C6-C60 aryl group.

In yet another embodiment, R and R' may each independently be a substituted or unsubstituted C6-C40 aryl group.

In yet another embodiment, R and R' may each independently be a C6-C40 monocyclic or polycyclic aryl group.

In yet another embodiment, R and R' may each independently be a C6-C20 monocyclic or polycyclic aryl group.

In yet another embodiment, R and R' may each independently be a C6-C20 monocyclic aryl group.

In yet another embodiment, R and R' may be phenyl groups.

前記グループＩＩにおいて、＊は、結合位置を意味する。 The substituted or unsubstituted C6 to C60 aryl group attached to the core of the compound represented by Formula 1 may be any one of the substituents in Group II below.

In the above Group II, * indicates the bonding position.

When the aryl group is a biphenyl or a substituted or unsubstituted fluorenyl group, a monoamine having two or more directly bonded aromatic groups and fluorenyl type substituents has high hole mobility and low drive value characteristics when used in a hole transport layer.

The aforementioned example compound may be represented by any one of the compounds in Group I below.

The above-mentioned compound or composition may be for use in an organic optoelectronic device, and the compound or composition for an organic optoelectronic device may be formed by a dry deposition method such as chemical vapor deposition.

Hereinafter, an organic optoelectronic device using the above-mentioned compound for organic optoelectronic devices or composition for organic optoelectronic devices will be described.

The organic optoelectronic element is not particularly limited as long as it is an element capable of converting electrical energy into light energy and vice versa, and examples thereof include organic photoelectric elements, organic light-emitting elements, organic solar cells, and organic photoconductor drums.

In one embodiment of the present application, an organic light-emitting device is provided that includes a first electrode, a second electrode provided opposite the first electrode, and one or more organic layers provided between the first electrode and the second electrode, and at least one of the organic layers includes a heterocyclic compound represented by Chemical Formula 1.

In one embodiment of the present application, the first electrode may be an anode and the second electrode may be a cathode.

In another embodiment, the first electrode may be a cathode and the second electrode may be an anode.

The specific details regarding the heterocyclic compound represented by Chemical Formula 1 are the same as those described above.

In one embodiment of the present application, the organic light-emitting device may be a blue organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the blue organic light-emitting device.

In one embodiment of the present application, the organic light-emitting device may be a green organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the green organic light-emitting device.

In one embodiment of the present application, the organic light-emitting device may be a red organic light-emitting device, and the heterocyclic compound represented by Chemical Formula 1 may be used as a material for the red organic light-emitting device.

The organic light-emitting device of the present invention can be manufactured by the usual manufacturing methods and materials for organic light-emitting devices, except that one or more organic layers are formed using the heterocyclic compound described above.

When manufacturing an organic light-emitting device, the heterocyclic compound is formed in an organic layer by a solution coating method as well as a vacuum deposition method. Here, the solution coating method means, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

Here, we will explain another example of an organic light-emitting element, which is an example of an organic optoelectronic element, with reference to the drawings.

Figures 1 to 3 show examples of the stacking order of electrodes and organic layers of an organic light-emitting device according to one embodiment of the present application. However, these drawings are not intended to limit the scope of the present application, and structures of organic optoelectronic devices known in the art are also applicable to the present application.

FIG. 1 shows an organic light-emitting device in which an anode 200, an organic layer 300, and a cathode 400 are sequentially stacked on a substrate 100. However, the present invention is not limited to this structure, and an organic light-emitting device in which a cathode, an organic layer, and an anode are sequentially stacked on a substrate as shown in FIG. 2 may also be realized.

Figure 3 illustrates an example in which the organic layer is multi-layered. The organic light-emitting device in Figure 3 includes a hole injection layer 301, a hole transport layer 302, an emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306. However, the scope of this application is not limited to such a laminated structure, and the remaining layers except for the emitting layer may be omitted as necessary, and other necessary functional layers may be further added.

The compound represented by the above chemical formula 1 can be used as a material for the electron transport layer, hole transport layer, and light emitting layer in an organic light emitting device.

The anode material may be a material having a relatively large work function, such as a transparent conductive oxide, a metal, or a conductive polymer. Specific examples of the anode material include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO ₂ :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, and polyaniline.

The cathode material may be a material having a relatively low work function, such as a metal, a metal oxide, or a conductive polymer, etc. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; and materials with a multilayer structure such as LiF/Al or LiO ₂ /Al.

As the hole injection material, a known hole injection material can be used, for example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Pat. No. 4,356,429, or a starburst type amine derivative described in the literature [Advanced Material, 6, p. 677 (1994)], for example, tris(4-carbazoyl-9-ylphenyl)amine (TCTA), 4,4',4"-tri[phenyl(m-tolyl)amino]triphenylamine (m-MTDATA), 1,3,5-tris[4-(3-methylphenylphenylamino)phenyl]benzene (m-MTDAPB), polyaniline/dodecylbenzenesulfonic acid (Polyaniline/Dodecylbenzenesulfonic acid), which is a soluble conductive polymer, or the like. acid), or poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate), polyaniline/camphor sulfonic acid, or polyaniline/poly(4-styrenesulfonate), etc. can be used.

As hole transport materials, pyrazoline derivatives, arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, etc. can be used, and low molecular weight or high molecular weight materials may also be used.

Examples of electron transport materials that can be used include oxadiazole derivatives, anthraquinodimethane and its derivatives, benzoquinone and its derivatives, naphthoquinone and its derivatives, anthraquinone and its derivatives, tetracyanoanthraquinodimethane and its derivatives, fluorenone derivatives, diphenyldicyanoethylene and its derivatives, diphenoquinone derivatives, and metal complexes of 8-hydroxyquinoline and its derivatives. Not only low molecular weight substances but also high molecular weight substances may be used.

As an electron injection material, for example, LiF is typically used in the industry, but this application is not limited to this.

As the luminescent material, red, green or blue luminescent materials can be used, and if necessary, two or more luminescent materials can be mixed and used. In this case, two or more luminescent materials can be deposited as individual supply sources or premixed and deposited as one supply source. In addition, a fluorescent material can be used as the luminescent material, but it can also be used as a phosphorescent material. As the luminescent material, a material that emits light by combining holes and electrons injected from the anode and cathode, respectively, can be used alone, or a material in which both the host material and the dopant material are involved in light emission can be used.

When using a mixture of hosts of light-emitting materials, hosts of the same type may be mixed and used, or hosts of different types may be mixed and used. For example, two or more types of N-type host materials or P-type host materials may be selected and used as the host material of the light-emitting layer.

The organic light-emitting device according to one embodiment of the present application may be a front-emitting type, a back-emitting type, or a dual-emitting type, depending on the materials used.

The above-mentioned embodiments will be described in more detail below through examples. However, the following examples are merely for illustrative purposes and do not limit the scope of the rights.

Unless otherwise specified, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or were synthesized by known methods.

(Production of compounds for organic optoelectronic devices)
[Production Example 1] Production of Intermediate A1

1) Preparation of intermediate A1-2 2,3-dibromothiophene (40g, 165.33mmol) and phenylboronic acid (48.38g, 396.79mmol) were dissolved in 500ml of toluene, 100ml of EtOH, and 100ml of _H2O , and then Pd( _PPh3 ) ₄ (3.82g, _3.31mmol ) and _K2CO3 (137.1g, 991.98mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, the mixture was extracted with MC and distilled water, and the organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain intermediate A1-2 (35g, 90%).

2) Preparation of Intermediate A1-1 Intermediate A1-2 (40 g, 169.25 mmol) was dissolved in 400 ml of DMF, and then NBS (33.14 g, 186.18 mmol) was added and stirred at room temperature for 4 hours. After the reaction was completed, the mixture was extracted with MC and distilled water, and the organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. The mixture was then purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain Intermediate A1-1 (50 g, 93%).

3) Preparation of intermediate A1 Intermediate A1-1 (50g, 158.61mmol) and bis(pinacolato)diboron (60.42g, 237.92mmol) were dissolved in 500ml of 1,4-dioxane, and then Pd(dppf) _Cl2 (2.32g, 3.17mmol) and KOAc (46.7g, 475.84mmol) were added and stirred under reflux for 8 hours. After the reaction was completed, the mixture was extracted with MC and water, and the organic layer was dried _over anhydrous MgSO4 and filtered through silica gel. Precipitation was performed with MC/MeOH. The precipitate was filtered to obtain intermediate A1 (51g, 89%).
Intermediate A was synthesized in the same manner as in Preparation Example 1, except that S1 in Table 1 below was used instead of 2,3-dibromothiophene and intermediate S2 was used instead of phenylboronic acid.

[Production Example 2] Production of Intermediate B1

1) Preparation of intermediate B1-2 2,3-diphenylthiophene (30 g, 126.94 mmol) was dissolved in 300 ml of chloroform, cooled to 0°C, and then bromine (42.6 g, 266.58 mmol) was slowly added and stirred for 3 hours. After the reaction was completed, the mixture was extracted with MC and distilled water, and the organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. The mixture was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain intermediate B1-2 (43 g, 86%).

2) Preparation of intermediate B1-1 Intermediate B1-2 (43 g, 109.1 mmol) was dissolved in 400 ml of anhydrous diethyl ether, cooled to -78°C, and n-BuLi (45.8 ml, 114.56 mmol) was slowly added and stirred for 1 hour. After the reaction was completed, the mixture was extracted with EA and diluted NH ₄ Cl aqueous solution, the organic layer was dried over anhydrous MgSO ₄ , the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain intermediate B1-1 (27 g, 78%).

3) Preparation of intermediate B1 Intermediate B1-1 (27 g, 85.65 mmol) and Bis(pinacolato)diboron (32.63 g, 128.48 mmol) were dissolved in 300 ml of 1,4-dioxane, and then Pd(dppf)Cl ₂ (2.51 g, 3.43 mmol) and KOAc (25.22 g, 256.96 mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, the mixture was extracted with MC and water, and the organic layer was dried over anhydrous MgSO ₄ and filtered through silica gel. Precipitation was performed with MC/MeOH. The precipitate was filtered to obtain intermediate B1 (26 g, 83%).
Intermediate B was synthesized in the same manner as in Preparation Example 2, except that S3 in Table 2 below was used instead of 2,3-diphenylthiophene.

[Production Example 3] Production of Compound 1

1) Preparation of Compound 1-4 5-bromo-2,3-diphenylthiophene (50 g, 158.61 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (38.23 g, 174.48 mmol) were dissolved in 500 ml of dioxane and 100 ml of H ₂ O, and then Pd(PPh ₃ ) ₄ (9.16 g, 7.93 mmol) and NaHCO ₃ (39.98 g, 475.84 mmol) were added and the mixture was refluxed and stirred for 14 hours. After the reaction was completed, MC was added to the reaction solution to dissolve it, and the solution was extracted with distilled water. The organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. The solution was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain compound 1-4 (41 g, 79%).

2) Preparation of Compound 1-3 Compound 1-4 (41 g, 125.21 mmol) was dissolved in 500 ml of MC, and TEA (38.01 g, 375.64 mmol) was added. After lowering the temperature to 0°C at room temperature, 4-bromobenzoyl chloride (30.23 g, 137.74 mmol) was dissolved in MC and slowly added dropwise. After the reaction was completed, the mixture was extracted with MC and distilled water, and the organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. Compound 1-3 (55 g, 86%) was obtained by purifying the mixture by column chromatography using dichloromethane and hexane as a developing solvent.

3) Preparation of Compound 1-2 Compound 1-3 (55 g, 107.75 mmol) was dissolved in 500 ml of nitrobenzene, and then POCl ₃ (18.17 g, 118.53 mmol) was slowly added dropwise, followed by stirring at 150° C. for 4 hours. After the reaction was completed, the mixture was neutralized with an aqueous NaHCO ₃ solution, extracted with MC and distilled water, and the organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Compound 1-2 (48 g, 90%) was obtained by purifying the mixture by column chromatography using dichloromethane and hexane as a developing solvent.

4) Preparation of Compound 1-1 Compound 1-2 (48 g, 97.48 mmol) and Bis(pinacolato)diboron (37.13 g, 146.21 mmol) were dissolved in 500 ml of 1,4-dioxane, and then Pd(dppf)Cl ₂ (2.85 g, 3.9 mmol) and KOAc (28.7 g, 292.43 mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, the mixture was extracted with MC and water, and the organic layer was dried over anhydrous MgSO ₄ and filtered through silica gel. Precipitation was performed with MC/MeOH. The precipitate was filtered to obtain compound 1-1 (46 g, 87%).

5) Preparation of Compound 1 Compound 1-1 (10g, 18.54mmol) and 4-(4-bromophenyl)-2,6-diphenylpyrimidine (7.54g, _19.46mmol ) were dissolved in 100ml of Tol, 20ml of EtOH, and 20ml of _H2O , and then Pd( _PPh3 ) ₄ (1.07g, 0.93mmol) and _K3PO4 (11.80g, 55.61mmol) were added and stirred under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and a solid was generated and filtered, then washed with EA and MeOH. The solid was then completely dissolved in an excess of dichloromethane and filtered through silica gel to obtain compound 1 (10g, 75%).
The target compound was synthesized in the same manner as in Preparation Example 3 except that Intermediate C in Table 3 below was used instead of 5-bromo-2,3-diphenylthiophene, Intermediate D was used instead of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, Intermediate E was used instead of 4-bromobenzoyl chloride, and Intermediate F was used instead of 4-(4-bromophenyl)-2,6-diphenylpyrimidine.

[Production Example 4] Production of Compound 376

Preparation of Compound 376-5 2,5-dibromothiophene (82.82 g, 342.33 mmol) and 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)aniline (50 g, 228.22 mmol) were dissolved in 500 ml of 1,4-dioxane and 100 ml of H ₂ O, and then Pd(PPh ₃ ) ₄ (7.91 g, 6.85 mmol) and NaHCO ₃ (57.52 g, 684.65 mmol) were added and the mixture was refluxed and stirred for 8 hours. After the reaction was completed, MC was added to the reaction solution to dissolve it, and then the solution was extracted with distilled water. The organic layer was dried over anhydrous _MgSO4 , the solvent was removed using a rotary evaporator, and the mixture was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain compound 376-5 (40 g, 69%).

Preparation of compound 376-4 Compound 376-5 (40 g, 157.39 mmol) was dissolved in 400 ml of MC, and TEA (47.78 g, 472.16 mmol) was added. After lowering the temperature to 0 ° C. at room temperature, benzoyl chloride (24.34 g, 173.13 mmol) was dissolved in MC and slowly added dropwise. After the reaction was completed, it was extracted with MC and distilled water, the organic layer was dried with anhydrous MgSO ₄ , the solvent was removed with a rotary evaporator, and the product was purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain compound 376-4 (45 g, 80%).

Preparation of Compound 376-3 Compound 376-4 (45 g, 125.61 mmol) was dissolved in 450 ml of nitrobenzene, and then POCl ₃ (21.19 g, 138.17 mmol) was slowly added dropwise, followed by stirring at 150° C. for 4 hours. After the reaction was completed, the mixture was neutralized with an aqueous NaHCO ₃ solution, extracted with MC and distilled water, and the organic layer was dried over anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Compound 376-3 (32 g, 75%) was obtained by purifying the mixture by column chromatography using dichloromethane and hexane as a developing solvent.

Preparation of Compound 376-2 Compound 376-3 (32 g, 94.05 mmol) and phenylboronic acid (12.04 g, 98.75 mmol) were dissolved in 300 ml of toluene, 60 ml of ethanol, and 60 ml of H ₂ O, and then Pd(PPh ₃ ) ₄ (5.43 g, 4.7 mmol) and K ₂ CO ₃ (39 g, 282.15 mmol) were added and stirred under reflux for 8 hours. After the reaction was completed, MC was added to the reaction solution and dissolved, and the solution was extracted with distilled water, and the organic layer was dried with anhydrous MgSO ₄ , and the solvent was removed using a rotary evaporator. Compound 376-2 (27 g, 85%) was obtained by purifying the compound by column chromatography using dichloromethane and hexane as a developing solvent.

Preparation of compound 376-1 Compound 376-2 (27 g, 80.01 mmol) was dissolved in 300 ml of chloroform, and the temperature was lowered to 0°C. Bromine (14.07 g, 88.02 mmol) was diluted in chloroform and slowly added dropwise. After the reaction was completed, the mixture was extracted with MC and distilled water, and the organic layer was dried over anhydrous _MgSO4 , and the solvent was removed using a rotary evaporator. Compound 376-1 (29 g, 87%) was obtained by purifying the product by column chromatography using dichloromethane and hexane as a developing solvent.

Preparation of Compound 376 Compound 376-1 (8 g, 19.22 mmol) and 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborol-2-yl)phenyl)-1,3,5-triazine (8.78 g, 20.18 mmol) were dissolved in 100 ml of toluene, 20 ml of ethanol, and 20 ml of H ₂ O, and then Pd(PPh ₃ ) ₄ (1.11 g, 0.96 mmol) and K ₂ CO ₃ (7.97 g, 57.76 mmol) were added and the mixture was refluxed and stirred for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solid was filtered and washed with EA and MeOH. The solid was then completely dissolved in excess dichloromethane and filtered through silica gel to give compound 376 (9.3 g, 75%).

In the above Production Example 4, intermediate G in Table 4 below was used instead of 2,5-dibromothiophene, intermediate H was used instead of phenylboronic acid, and intermediate I was used instead of 2,4-diphenyl-6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1,3,5-triazine, and the target compound was synthesized in the same manner.

The compounds were produced using the methods described in the above production examples, and the results of synthesis confirmation are shown in Tables 5 and 6 below.

<Experimental Example 1> Fabrication of Organic Light-Emitting Device <Comparative Examples 1-1 to 1-3 and Examples 1 to 53>
1) Preparation of an organic light-emitting element A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.
Next, the ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine: 2-TNATA) was placed in a cell in the vacuum deposition apparatus.

このように正孔注入層および正孔輸送層を形成させた後、その上に発光層として次の構造の青色発光材料を蒸着させた。具体的には、真空蒸着装置内の一方のセルに青色発光ホスト材料であるＨ１を２００Åの厚さに真空蒸着させ、その上に青色発光ドーパント材料であるＤ１をホスト材料対比５％真空蒸着させた。

次いで、電子輸送層として前記表６に表されている化合物を３００Åの厚さに蒸着した。

電子注入層としてリチウムフルオライド（ｌｉｔｈｉｕｍ ｆｌｕｏｒｉｄｅ：ＬｉＦ）を１０Åの厚さに蒸着し、Ａｌ陰極を１，０００Åの厚さにしてＯＬＥＤ素子を作製した。
一方、ＯＬＥＤ素子の作製に必要なすべての有機化合物は、材料ごとにそれぞれ１０^－６～１０^－８ｔｏｒｒ下で真空昇華精製して、ＯＬＥＤの作製に使用した。 Next, the chamber was evacuated until the degree of vacuum in the chamber reached 10 ⁻⁶ torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer having a thickness of 600 Å on the ITO substrate.
N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate the NPB, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

After the hole injection layer and the hole transport layer were formed in this manner, a blue light-emitting material having the following structure was deposited thereon as a light-emitting layer. Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of a vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon in an amount of 5% relative to the host material.

Then, the compound shown in Table 6 above was evaporated as an electron transport layer to a thickness of 300 Å.

An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as an electron injection layer and forming an Al cathode to a thickness of 1,000 Å.
On the other hand, all organic compounds required for the fabrication of OLED elements were purified by vacuum sublimation under 10 ⁻⁶ to 10 ⁻⁸ torr for each material, and used in the fabrication of OLEDs.

2) Driving voltage and luminous efficiency of organic light emitting device The electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured using M7000 manufactured by Mac Science, and _T95 at a reference luminance of 700 cd/ ^m2 was measured using a lifetime measuring device (M6000) manufactured by Mac Science based on the measurement results. The driving voltage, luminous efficiency, external quantum efficiency, and color coordinates (CIE) of the white organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 7.

As can be seen from the results in Table 7, the organic light emitting device using the electron transport layer material of the blue organic light emitting device of the present invention had a lower driving voltage and significantly improved luminous efficiency and lifetime compared to Comparative Example 1. In particular, it was confirmed that Compounds 6, 10, 36, 181, 242, 376, 421, 481, 541, and 856 were excellent in all aspects of driving, efficiency, and lifetime.
The reason for this result is believed to be that when the invented compound having suitable length, strength and flat properties is used as an electron transport layer, it receives electrons under certain conditions to form an excited state compound, and in particular, when an excited state of the hetero skeleton part of the compound is formed, the excited energy should be transferred to a stable state before the excited hetero skeleton part undergoes other reactions, and the relatively stable compound can efficiently transport electrons without decomposition or destruction of the compound. For reference, it is considered that those having a stable state when excited are aryl or acene compounds or multi-membered ring hetero compounds. Therefore, it is believed that the compound of the present invention has improved electron-transport properties or improved stability, resulting in excellence in all aspects of operation, efficiency and life.

<Experimental Example 2> Fabrication of organic light-emitting element <Comparative Example 2>
1) Preparation of an organic light-emitting element A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.
Next, the ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine: 2-TNATA) was deposited by vapor deposition in a cell in the vacuum deposition apparatus.

このように正孔注入層および正孔輸送層を形成させた後、その上に発光層として次の構造の青色発光材料を蒸着させた。具体的には、真空蒸着装置内の一方のセルに青色発光ホスト材料であるＨ１を２００Åの厚さに真空蒸着させ、その上に青色発光ドーパント材料であるＤ１をホスト材料対比５％真空蒸着させた。

次いで、電子輸送層として下記構造式Ｅ１の化合物を３００Åの厚さに蒸着した。

電子注入層としてリチウムフルオライド（ｌｉｔｈｉｕｍ ｆｌｕｏｒｉｄｅ：ＬｉＦ）を１０Åの厚さに蒸着し、Ａｌ陰極を１，０００Åの厚さにしてＯＬＥＤ素子を作製した。
一方、ＯＬＥＤ素子の作製に必要なすべての有機化合物は、材料ごとにそれぞれ１０^－６～１０^－８ｔｏｒｒ下で真空昇華精製して、ＯＬＥＤの作製に使用した。 Next, the chamber was evacuated until the degree of vacuum in the chamber reached 10 ⁻⁶ torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer having a thickness of 600 Å on the ITO substrate.
N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate the NPB, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

After the hole injection layer and the hole transport layer were formed in this manner, a blue light-emitting material having the following structure was deposited thereon as a light-emitting layer. Specifically, a blue light-emitting host material H1 was vacuum-deposited in one cell of a vacuum deposition apparatus to a thickness of 200 Å, and a blue light-emitting dopant material D1 was vacuum-deposited thereon in an amount of 5% relative to the host material.

Then, a compound represented by the following structural formula E1 was deposited to a thickness of 300 Å as an electron transport layer.

An OLED device was fabricated by depositing lithium fluoride (LiF) to a thickness of 10 Å as an electron injection layer and forming an Al cathode to a thickness of 1,000 Å.
On the other hand, all organic compounds necessary for the fabrication of OLED elements were purified by vacuum sublimation under 10 ⁻⁶ to 10 ⁻⁸ torr for each material, and used in the fabrication of OLEDs.

<Examples 54 to 63>
An organic electroluminescent device was fabricated in the same manner as in Comparative Example 2, except that an electron transport layer E1 was formed to a thickness of 250 Å, and then a hole blocking layer was formed on the electron transport layer using the compound shown in Table 8 to a thickness of 50 Å.
The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the blue organic light emitting device manufactured according to the present invention were measured, and the results are shown in Table 8.

As can be seen from the results in Table 8, the organic electroluminescent device using the hole blocking layer material of the blue organic electroluminescent device of the present invention had a lower driving voltage and significantly improved luminous efficiency and life span compared to Comparative Example 2.

<Experimental Example 3> Fabrication of organic light-emitting element <Comparative Example 3>
1) Preparation of an organic light-emitting element A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.
Next, the ITO substrate was placed in a substrate holder of a vacuum deposition apparatus, and the following 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine: 2-TNATA) was placed in a cell in the vacuum deposition apparatus.

このように正孔注入層および正孔輸送層を形成させた。
その上に発光層を、ホストとしてＨ２と、緑色燐光ドーパントとしてＩｒ（ｐｐｙ）_３を７％ドーピングして４００Å蒸着した。

以後、正孔阻止層としてＢＣＰを６０Å蒸着し、その上に電子輸送層としてＡｌｑ３を２００Å蒸着した。最後に、電子輸送層上にリチウムフルオライド（ｌｉｔｈｉｕｍ ｆｌｕｏｒｉｄｅ：ＬｉＦ）を１０Åの厚さに蒸着して電子注入層を形成した後、電子注入層上にアルミニウム（Ａｌ）陰極を１，２００Åの厚さに蒸着して陰極を形成することにより、有機電界発光素子を製造した。
一方、ＯＬＥＤ素子の作製に必要なすべての有機化合物は、材料ごとにそれぞれ１０^－６～１０^－８ｔｏｒｒ下で真空昇華精製してＯＬＥＤの作製に使用した。 Next, the chamber was evacuated until the degree of vacuum in the chamber reached 10 ⁻⁶ torr, and then a current was applied to the cell to evaporate 2-TNATA, thereby depositing a hole injection layer having a thickness of 600 Å on the ITO substrate.
N,N'-bis(α-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell in the vacuum deposition apparatus, and a current was applied to the cell to evaporate the NPB, thereby depositing a hole transport layer having a thickness of 300 Å on the hole injection layer.

In this manner, a hole injection layer and a hole transport layer were formed.
An emitting layer was deposited thereon to a thickness of 400 Å using H2 as a host and 7% doping of Ir(ppy) ₃ as a green phosphorescent dopant.

Then, BCP was deposited to a thickness of 60 Å as a hole blocking layer, and Alq3 was deposited to a thickness of 200 Å thereon as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic electroluminescent device.
On the other hand, all organic compounds necessary for the production of OLED elements were purified by vacuum sublimation under 10 ⁻⁶ to 10 ⁻⁸ torr for each material and used for the production of OLEDs.

<Examples 64 to 69>
An organic electroluminescent device was prepared in the same manner as in Comparative Example 3, except that the compound shown in Table 9 was used instead of H2 used in forming the host in Comparative Example 3.
The driving voltage, luminous efficiency, color coordinate (CIE), and lifetime of the green organic light emitting device prepared according to the present invention were measured, and the results are shown in Table 9.

<Experimental Example 4> Fabrication of Organic Light-Emitting Device <Comparative Example 4 and Examples 70 to 79>
1) Preparation of an organic light-emitting element A transparent electrode ITO thin film obtained from OLED glass (manufactured by Samsung Corning) was ultrasonically cleaned using trichloroethylene, acetone, ethanol, and distilled water in that order for 5 minutes each, and then stored in isopropanol before use.
Organic materials were formed on the ITO transparent electrode (anode) in a two-stack WOLED (White Organic Light Device) structure. In the first stack, TAPC was first thermally vacuum deposited to a thickness of 300 Å to form a hole transport layer. After the hole transport layer was formed, an emitting layer was thermally vacuum deposited thereon as follows. The emitting layer was deposited to a thickness of 300 Å by doping 8% FIrpic as a blue phosphorescent dopant into the host TCz1. The electron transport layer was formed to a thickness of 400 Å using TmPyPB, and then the charge generation layer was formed to a thickness of 100 _Å by doping 20% _Cs2CO3 into the compound shown in Table 10 below.
The second stack was formed by first thermal vacuum depositing _MoO3 to a thickness of 50 Å to form a hole injection layer. The hole transport layer, which is a common layer, was formed by doping 20% _MoO3 into TAPC to form a 100 Å thickness, and then depositing TAPC to form a 300 Å thickness. On top of that, the light emitting layer was formed by doping 8% Ir(ppy) ₃ , a green phosphorescent dopant, into the host TCz1 to form a 300 Å thickness, and then using TmPyPB to form a 600 Å thickness as an electron transport layer. Finally, lithium fluoride (LiF) was deposited to a thickness of 10 Å on the electron transport layer to form an electron injection layer, and then an aluminum (Al) cathode was deposited to a thickness of 1,200 Å on the electron injection layer to form a cathode, thereby manufacturing an organic light emitting device.

On the other hand, all organic compounds required for the fabrication of OLED elements were purified by vacuum sublimation under 10 ⁻⁶ to 10 ⁻⁸ torr for each material, and used in the fabrication of OLEDs.

The driving voltage, luminous efficiency, color coordinates (CIE), and lifetime of the white organic light-emitting device manufactured according to the present invention were measured, and the results are shown in Table 10.

As can be seen from the results in Table 10, the organic electroluminescence device using the charge generation layer material of the two-stack white organic electroluminescence device of the present invention had a lower driving voltage and improved luminous efficiency compared to Comparative Example 3. The reason for this result is presumed to be that the compound of the present invention used as the N-type charge generation layer, which is composed of the invented skeleton having appropriate length, strength, and flatness characteristics and an appropriate hetero compound capable of binding with metal, is doped with an alkali metal or alkaline earth metal to form a gap state in the N-type charge generation layer, and it is believed that electrons generated from the P-type charge generation layer are easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. Therefore, it is believed that the P-type charge generation layer can successfully inject and transport electrons into the N-type charge generation layer, which results in a lower driving voltage of the organic electroluminescence device and improved efficiency and lifespan.

Although the preferred embodiment of the present invention has been described in detail above, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

100: Substrate 200: Anode 300: Organic layer 301: Hole injection layer 302: Hole transport layer 303: Light-emitting layer 304: Hole blocking layer 305: Electron transport layer 306: Electron injection layer 400: Cathode

Claims (5)

A compound represented by any one of the following chemical formulas 2 to 4:

In the above Chemical Formulas 2 to 4,
^X1 is -O-; or -S-;
Ar ¹ to Ar ⁵ are each independently hydrogen; deuterium; a cyano group; -P(=O)RR'; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L ¹ to L ³ are each independently a single bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
^L4 and ^L5 are each independently a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group;
R and R' are each independently hydrogen; a substituted or unsubstituted C1-C60 alkyl group; a substituted or unsubstituted C6-C60 aryl group; or a substituted or unsubstituted C2-C60 heteroaryl group;
n1 to n5 are each independently an integer from 1 to 4;
At least one of Ar ¹ to Ar ⁵ is a substituent having electronic properties; or a substituent having hole properties;
the substituent having hole properties is a substituted or unsubstituted C6 to C60 aryl group having hole properties, a substituted or unsubstituted C2 to C60 heteroaryl group having hole properties, a substituted or unsubstituted arylamine group, or a substituted or unsubstituted heteroarylamine group;
The substituted or unsubstituted C6-C60 aryl group having hole properties is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted spiro-fluorenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted perylenyl group;
The substituted or unsubstituted C2 to C60 heteroaryl group having hole characteristics is any one of the following formulas 5-1 to 5-4:

In the above Chemical Formula 5-1 to Chemical Formula 5-4, X is -O- or -S-, and R ^b to R ^e are hydrogen, deuterium, a cyano group, or a substituted or unsubstituted C1 to C60 alkyl group;
The substituent having electronic properties is a substituted or unsubstituted C2-C60 heteroaryl group having electronic properties;
The substituted or unsubstituted C2-C60 heteroaryl group having the electronic properties is a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted tetrazolyl group, a substituted or unsubstituted quinolinylene group, a substituted or unsubstituted isoquinolinylene group, a substituted or unsubstituted pyridinylene group, a substituted or unsubstituted pyrimidinylene group, a substituted or unsubstituted triazinylene group, a substituted or unsubstituted furanyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted isofuranyl group, a substituted or unsubstituted benzoisofuranyl group, a substituted or unsubstituted oxazoline group, a substituted or unsubstituted benzoxazoline group, a substituted or unsubstituted oxadiazoline group, a substituted or unsubstituted benzoxadiazoline group, a substituted or unsubstituted oxatriazolyl group. , a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazoline group, a substituted or unsubstituted benzoisothiazoline group, a substituted or unsubstituted thiazoline group, a substituted or unsubstituted benzothiazoline group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted benzopyridazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted benzopyrazinyl group, a substituted or unsubstituted phthalazinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted phenazinyl group, or a combination thereof;
"Substituted or unsubstituted" means substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium; -CN; -P(=O)RR'; a C1-C20 linear or branched alkyl group; a C6-C60 monocyclic or polycyclic aryl group; and a C2-C60 monocyclic or polycyclic heteroaryl group. A compound that is any one of the following Group I compounds:

an anode and a cathode facing each other;
at least one organic layer located between the anode and the cathode;
An organic optoelectronic device, wherein the organic layer comprises a compound according to claim 1 or 2. the organic layer comprises an electron transport layer, a charge generating layer, a hole blocking layer, or a combination thereof;
The organic optoelectronic device of claim 3 , wherein the electron transport layer, charge generation layer, or hole blocking layer comprises the compound. A display device including the organic optoelectronic element according to claim 3.

Images